Contours are useful for creating a map. They have a couple of fun properties:

(1) Water naturally goes perpendicular to the contours. Perpendicular to a contour is the path of steepest descent/ascent.

(2) Paths made by living things usually intersect contours at some maximum angle that will depend on local topography. The closer the contours (steeper the slope), the shallower that the crossing angle of roads, railroads, aqueducts, and so on will make with that contour because critters are lazy and wheels/hooves tend to slip on too steep of a slope. If a path exactly follows a contour, then it's just like living on flat land except for the going in circles part.

I mention this because you have a number of roads that would be very steep in places. That road from the fort to hospital would probably be a wonderful slide in wet weather and a difficult thing to use in normal times. A cog railway typically follows the path of steepest ascent, so that might work.